Stereoselective synthesis of benzannulated spiroketals: Influence of the aromatic ring on reactivity and conformation Journal Article

   


Authors: Liu, G.; Wurst, J. M.; Tan, D. S.
Article Title: Stereoselective synthesis of benzannulated spiroketals: Influence of the aromatic ring on reactivity and conformation
Abstract: Image Presented A systematic stereocontrolled synthesis of benzannulated spiroketals has been developed, using kinetic spirocyclization reactions of glycal epoxides, leading to a new AcOH-induced cyclization and valuable insights into the reactivity and conformations of these systems. One stereochemical series accommodates axial positioning of the aromatic ring while another adopts an alternative <sup>1</sup>C<sub>4</sub> chair conformation to avoid it. Equatorial aromatic rings also participate in nonobvious steric interactions that impact thermodynamic stability. A discovery library of 68 benzannulated spiroketals with systematic variations in stereochemistry, ring size, and positioning of the aromatic substituent has been synthesized for broad biological evaluation. © 2009 American Chemical Society.
Keywords: structure activity relation; structure-activity relationship; chemistry; kinetics; thermodynamics; chemical structure; molecular structure; catalysis; heterocyclic compounds; heterocyclic compound; synthesis; stereoisomerism; benzene derivative; furan derivative; spiro compound; spiroketal; combinatorial chemistry; benzene derivatives; combinatorial chemistry techniques; furans; spiro compounds
Journal Title: Organic Letters
Volume: 11
Issue: 16
ISSN: 1523-7060
Publisher: American Chemical Society  
Date Published: 2009-08-20
Start Page: 3670
End Page: 3673
Language: English
DOI: 10.1021/ol901437f
PUBMED: 19634891
PROVIDER: scopus
PMCID: PMC2760470
DOI/URL:

http://www.scopus.com/inward/record.url?eid=2-s2.0-68949184356&partnerID=40&md5=aa8e9f9c1e849381aceea753c85dafbc
Notes: --- - "Cited By (since 1996): 7" - "Export Date: 30 November 2010" - "Source: Scopus"
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MSK Authors
  1. Guodong Liu
    2 Liu
  2. Derek S Tan
    92 Tan
  3. Jacqueline M Wurst
    5 Wurst
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